This invention relates to cyclic amides substituted at the .alpha.-position with various aryl groups, their agriculturally suitable salts and compositions, and methods of their use as general or selective fungicides.
EP-A-398,692 disclosed amides of Formula i as fungicides for crop protection. Compounds of Formula i are: ##STR2##
wherein
R.sup.1 and R.sup.2 are each hydrogen, lower alkyl, or lower cycloalkyl. PA0 W is ##STR4## PA0 A is O; S; N; NR.sup.5 ; or CR.sup.14 ; PA0 G is C or N; provided that when G is N, A is N or CR.sup.14 and the floating double bond is attached to A; PA0 W is O or S; PA0 X is OR.sup.1 ; S(O).sub.m R.sup.1 ; or halogen; PA0 R.sup.1, R.sup.2, and R.sup.5 are independently H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 haloalkynyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.2 -C.sub.4 alkylcarbonyl, C.sub.2 -C.sub.4 alkoxycarbonyl; or benzoyl optionally substituted with R.sup.13 ; PA0 R.sup.3 and R.sup.4 are each independently H; halogen; cyano; nitro; C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkoxy; C.sub.2 -C.sub.6 alkenyloxy; or C.sub.2 -C.sub.6 alkynyloxy; PA0 Y is --O--; S(O).sub.n --; --CHR.sup.6 CHR.sup.6 --; --CR .sup.6 .dbd.CR.sup.6 --; --CHR.sup.6 O--; --OCHR.sup.6 --; --CHR.sup.6 S(O).sub.n --; --S(O).sub.n CHR.sup.6 --; --CHR.sup.6 ON.dbd.C(R.sup.7)--; --(R.sup.7)C.dbd.N--OCH(R.sup.6)--; --C(R.sup.7).dbd.N--O--; --O--N.dbd.C(R.sup.7)--; --CHR.sup.6 OC(.alpha.O)N(R.sup.15)--; or a direct bond; and the directionality of the Y linkage is defined such that the moiety depicted on the left side of the linkage is bonded to the phenyl ring and the moiety on the right side of the linkage is bonded to Z; PA0 R.sup.6 is independently H or C.sub.1 -C.sub.3 alkyl; PA0 R.sub.7 is H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkoxy; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.2 -C.sub.4 alkylcarbonyl; C.sub.2 -C.sub.4 alkoxycarbonyl; cyano; or morpholinyl; PA0 Z is C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, or C.sub.2 -C.sub.10 alkynyl each optionally substituted with R.sup.8 ; or Z is C.sub.3 -C.sub.8 cycloalkyl or phenyl each optionally substituted with on of R.sup.9, R.sup.10, or both R.sup.9 and R.sup.10 ; or Z is a 3 to 14-membered nonaromatic heterocyclic ring system selected from the group monocyclic ring, fused bicyclic ring and fused tricyclic ring, or Z is a 5 to 14-membered aromatic heterocyclic ring system selected from the group monocyclic ring, fused bicyclic ring and fused tricyclic ring, each nonaromatic or aromatic ring system containing 1 to 6 heteroatoms independently selected from the group 1-4 nitrogen, 1-2 oxygen, and 1-2 sulfur, each nonaromatic or aromatic ring system optionally substituted with on of R.sup.9, R.sup.10, or both R.sup.9 and R.sup.10 ; or PA0 R.sup.7 and Z are taken together to form CH.sub.2 CH.sub.2 CH.sub.2, CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2, CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2, each CH.sub.2 group optionally substituted with 1-2 halogen; or PA0 Y and Z are taken together to form ##STR7## R.sup.3, Y and Z are taken together with the phenyl ring to form a naphthalene ring substituted on either ring with a floating R.sup.4 ; provided that when R.sup.3, Y, and Z are taken together with the phenyl ring to form a napthylene ring substituted by R.sup.4, and A is S, W is O, X is SCH.sub.3 and R.sup.2 is CH.sub.3 ; then R.sup.4 is other than H; PA0 J is --CH.sub.2 --; --CH.sub.2 CH .sub.2 --; --OCH.sub.2 ; --CH.sub.2 O--; --SCH.sub.2 --; --CH.sub.2 S--; --N(R.sup.16)CH.sub.2 --; or --CH.sub.2 N(R.sup.16)--; each CH.sub.2 group optionally substituted with 1 to 2 CH.sub.3 ; PA0 R.sup.8 is 1-6 halogen; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkoxy; C.sub.1 -C.sub.6 alkylthio; C.sub.1 -C.sub.6 haloalkylthio; C.sub.1 -C.sub.6 alkylsulfinyl; C.sub.1 -C.sub.6 alkylsulfonyl; C.sub.3 -C.sub.6 alkylthio; C.sub.1 -C.sub.6 cycloalkyl; C.sub.3 -C.sub.6 alkenyloxy; CO.sub.2 (C.sub.1 -C.sub.6 alkyl); NH(C.sub.1 -C.sub.6 alkyl); N(C.sub.1 -C.sub.6 alkyl).sub.2 ; cyano; or nitro; or R.sup.8 is phenyl, phenoxy, pyridinyl, pyridinyloxy, thienyl, furanyl, pyrimidinyl, or pyrimidinyloxy each optionally substituted with one of R.sup.11, R.sup.12, or both R.sup.11 and R.sup.12 ; PA0 R.sup.9 is 1-2 halogen; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkoxy; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.1 -C.sub.6 alkylthio; C.sub.1 -C.sub.6 haloalkylthio; C.sub.1 -C.sub.6 alkylsulfinyl; C.sub.1 -C.sub.6 alkylsulfonyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.3 -C.sub.6 alkenyloxy; C).sub.2 (C.sub.1 -C.sub.6 alkyl); NH(C.sub.1 -C.sub.6 alkyl); N(C.sub.1 -C.sub.6 alkyl).sub.2 ; --C(R.sup.18).dbd.NOR.sup.17 ; cyano; or nitro; or R.sup.9 is phenyl, benzyl, benzoyl, phenoxy, pyridinyl, pyridinyloxy, thienyl, thienyloxy, furanyl, pyrimidinyl, or pyrimidinyloxy each optionally substituted with on of R.sup.11, R.sup.12, or both R.sup.11 and R.sup.12 ; PA0 R.sup.10 is halogen; C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 haloalkyl; C.sub.1 -C.sub.4 alkoxy; nitro; or cyano; or PA0 R.sup.9 and R.sup.10, when attached to adjacent atoms, are taken together as --)CH.sub.2 O-- or --OCH.sub.2 CH.sub.2 O--; each CH.sub.2 group optionally substituted with 1-2 halogen; PA0 R.sup.11 and R.sup.12 are each independently halogen; C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 haloalkyl; C.sub.1 -C.sub.4 alkoxy; C.sub.1 -C.sub.4 haloalkoxy; nitro; or cyano; PA0 R.sub.13 is halogen; C.sub.1 -C.sub.3 alkyl; C.sub.1 -C.sub.3 haloalkyl; C.sub.1 -C.sub.3 alkoxy; C.sub.1 -C.sub.3 haloalkoxy; nitro; or cyano; PA0 R.sup.14 is H; halogen; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; or C.sub.3 -C.sub.6 cycloalkyl; PA0 R.sup.15, R.sup.16, R.sup.17, and R.sup.18 are each independently H; C.sub.1 -C.sub.3 alkyl; or phenyl optionally substituted with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, nitro or cyano; PA0 m, n, and q are each independently 0, 1 or 2; and PA0 P and r are each independently 0 or 1. PA0 W is O; PA0 R.sup.1 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 haloalkyl; PA0 R.sup.2 is H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; or C.sub.3 -C.sub.6 cycloalkyl; PA0 R.sup.3 and R.sup.4 are each independently H; halogen; cyano; nitro; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -C.sub.6 alkoxy; or C.sub.1 -C.sub.6 haloalkoxy; PA0 Y is --O--; --CH .dbd.CH --; --CH.sub.2 O--; --OCH.sub.2 --; --CH.sub.2 S(O).sub.n --; --CH.sub.2 O--N.dbd.C(R.sup.7)--; --C(R.sup.7).dbd.N--O--; --CH.sub.2 OC(O)NH--; or a direct bond; PA0 R.sup.7 is H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 alkynyl; or cyano; PA0 Z is C.sub.1 -C.sub.10 alkyl optionally substituted with R.sup.8 ; or C.sub.3 -C.sub.8 alkynyl; or cyano; PA0 Z is C.sub.1 -C.sub.10 alkyl optionally substituted with R.sup.8 ; or C.sub.3 -C.sub.8 cycloalkyl or phenyl, each optionally substituted with one of R.sup.9, R.sup.10, or bother R.sup.9 and R.sup.10 ;or Z is ##STR8## each group is optionally substituted with on R.sub.9, R.sub.10, or both R.sup.9 and R.sup.10 ; or PA0 R.sup.3, Y, and Z are taken together with the phenyl ring to form a naphthalene ring substituted on either ring with a floating R.sup.4 ; or PA0 Y and Z are taken together to form ##STR9## R.sup.8 is 1-6 halogen; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkoxy; or R.sup.8 is phenyl, phenoxy, pyridinyl, pyridinyloxy, pyrimidinyl, or pyrimidinyloxy each optionally substituted with one of R.sup.11, R.sup.12, or both R.sup.11 and R.sup.12 ; PA0 R.sup.9 is 1-2 halogen; C.sub.1 -C.sub.6 alkyl C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkoxy; C.sub.1 -C.sub.6 alkylthio; cyano; CO.sub.2 (C.sub.1 -C.sub.6 alkyl; NH(C.sub.1 -C.sub.6 alkyl; or N(C.sub.1 -C.sub.6 alkyl).sub.2 ; or R.sup.9 is C.sub.3 -C.sub.6 cycloalkyl, phenyl, phenoxy, pyridinyl, pyridinyloxy, pyrimidinyl, or pyrimidinyloxy each optionally substituted with one of R.sup.11, R.sup.12, or both R.sup.11 and R.sup.12, and PA0 R.sup.19 is H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; or phenyl optionally substituted with halogen, C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, nitro or cyano. PA0 Z is phenyl or Z-1 to Z-21, each optionally substituted with one of R.sup.9, R.sup.10, or both R.sup.9 and R.sup.10 ; or PA0 Y and Z are taken together to form ##STR10## J is --CH.sub.2 -- or --CH.sub.2 CH.sub.2 --; p is 0; and PA0 r is 1. PA0 A is O; N; NR.sup.5 ; or CR.sup.14 ; PA0 X is OR.sup.1 ; PA0 R.sup.1 is C.sub.1 -C.sub.3 alkyl; PA0 R.sup.2 is H or C.sub.1 -C.sub.2 alkyl; PA0 R.sup.3 and R.sup.4 are each H; PA0 Y is --O--; --CH.dbd.CH--; --CH.sub.2 O--; --OCH.sub.2 --; --CH.sub.2 O--N.dbd.C(R.sup.7)--; or --CH.sub.2 OC(.dbd.O)NH--; PA0 R.sup.7 is H; C.sub.1 -C.sub.3 alkyl; or C.sub.1 -C.sub.3 haloalkyl; and PA0 Z is phenyl, pyridinyl, pyrimidinyl, or thienyl, each optionally substituted with one of R.sup.9, R.sup.10, or both R.sup.9 and R.sup.10. PA0 A is O or NR.sup.5 ; PA0 G is C; PA0 Y is --O--; --CH.sub.2 O--;--OCH.sub.2 ; or --CH.sub.2 O--N.dbd.C(R.sup.7)--; and PA0 R.sup.7 is H; C.sub.1 -C.sub.2 alkyl; or C.sub.1 -C.sub.2 haloalkyl. PA0 A is N OR CR.sup.14 ; PA0 G is N; PA0 Y is --O--; --CH.sub.2 O--; or --CH.sub.2O--N.dbd.C(R.sup.7)--; and PA0 R.sup.7 is H; C.sub.1 -C.sub.2 alkyl; or C.sub.1 -C.sub.2 haloalkyl. PA0 R.sup.1 is methyl; PA0 R.sup.2 is methyl; and PA0 Z is phenyl optionally substituted with on of R.sup.9, R.sup.10, or both R.sup.9 and R.sup.10. PA0 R.sup.1 is methyl; PA0 R.sup.2 is methyl; and PA0 Z is phenyl optionally substituted with one of R.sup.9, R.sup.10, or both R.sup.9 and R.sup.10.
All the compounds disclose din EP-A-398,692 have an aryl moiety bonded to an acyclic alkoxyiminoacetamide group. The cyclic amides of the present invention are not disclosed therein.
WO 93/07116 disclosed compounds of Formula ii as fungicides for crop protection. Compounds of Formula ii are: ##STR3##
wherein:
Once again, the cyclic amides of this invention are not disclosed therein.
J. Heterocyclic Chem., (1987),24, 465, J. Heterocyclic Chem., (1988),25, 1307, and Australian J. Chem., (1977),30(8), 1815 disclose 4-nitrophenyl isoxazoles (iii), phenyl pyrazolones (iv), and aryl isothiazolinones (v) respectively. ##STR5##
However, no utility as fungicides is alleged and no ortho-substituted compounds of the present invention are disclosed.